Ammonia → 6-methyl-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one

HRID 550645Notes

Reaction equation

HRID 550645 reaction equation
[N:1]([CH:4]([CH3:11])[CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)=[C:2]=[O:3].N>C(Cl)Cl>[CH3:11][CH:4]1[NH:1][C:2](=[O:3])[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 217537131082916-60-6

Product 1

HCID 218153376-methyl-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-oneYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To PPA (15 ml) a solution of 2-(2-isocyanatopropyl)-thiophene in CH2Cl2 (15 ml) was added. The reaction mixture was stirred under reflux for 3 h, cooled, poured into ice and alkalified with concentrated ammonia. Then, the mixture was extracted with chloroform, dried over Na2SO4 and concentrated on rotary evaporator. The residue was purified by flash column chromatography on silica gel (eluent: chloroform/acetone—0→30%) to give 0.5 g of the target compound as a white solid.

Workup

  1. temperatureunder reflux for 3 h
  2. temperaturecooled
  3. additionpoured into ice
  4. extractionThen, the mixture was extracted with chloroform
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated on rotary evaporator
  7. customThe residue was purified by flash column chromatography on silica gel (eluent: chloroform/acetone—0→30%)

Sources & evidence

ORD record
ord-0b432daef3bb455abcf65a68ee96d7bd
Source dataset
uspto-grants-2011_05
Patent number
US07947689B2

Reaction notes

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